| 1. Round | 16/08/1999 | Karlsruher SC | - | VfL Bochum | 1:3 | ||||
| 2. Round | 21/08/1999 | TeBe Berlin | - | Karlsruher SC | 2:2 | ||||
| 3. Round | 30/08/1999 | Karlsruher SC | - | Bor. Mönchengladbach | 3:0 |  |
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| 4. Round | 10/09/1999 | Waldhof Mannheim | - | Karlsruher SC | 1:1 | ||||
| 5. Round | 17/09/1999 | Karlsruher SC | - | Kickers Offenbach | 1:1 | |
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| 6. Round | 25/09/1999 | Fortuna Köln | - | Karlsruher SC | 2:3 | ||||
| 9. Round | 24/10/1999 | Karlsruher SC | - | Chemnitzer FC | 1:2 | ||||
| 11. Round | 06/11/1999 | Energie Cottbus | - | Karlsruher SC | 3:2 | ||||
| 12. Round | 21/11/1999 | Karlsruher SC | - | Alemannia Aachen | 0:0 | ||||
| 14. Round | 06/12/1999 | Karlsruher SC | - | 1. FC Köln | 0:0 | ||||
| 16. Round | 15/12/1999 | Karlsruher SC | - | SpVgg Greuther Fürth | 0:1 | ||||
| 17. Round | 02/03/2000 | Stuttgarter Kickers | - | Karlsruher SC | 2:1 |  |
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| 21. Round | 06/03/2000 | Karlsruher SC | - | Waldhof Mannheim | 1:1 | ||||
| 23. Round | 19/03/2000 | Karlsruher SC | - | Fortuna Köln | 2:1 | ||||
| 25. Round | 02/04/2000 | Karlsruher SC | - | 1. FC Nürnberg | 0:1 |
Germany